50 Years of the Playboy Interview: Howard Stern

In 1962, future Pulitzer Prize–winning author Alex Haley sat down with jazz musician Miles Davis for what would become an institution of American journalism—the Playboy Interview. To celebrate the Interview’s 50th anniversary, Playboy has culled 50 of its most (in)famous Interviews and will publish them over the course of 50 weekdays (from September 4, 2012 to November 12, 2012) via Amazon’s Kindle Direct platform. Here, a glimpse at our conversation with radio personality Howard Stern from the April 1994 issue.

“I think free speech is the single greatest freedom we have in this country. For anyone to say that something shouldn’t be said hurts that freedom. The rule I follow is this: I should say anything that I think is funny.”

“My penis size has shaped a lot of things. I know that I would be the type of guy who would be in public showers if I had a big cock. Growing up as a kid, I never participated in sports because I didn’t want to take showers and have guys see my penis. Even a simple thing like going to a urinal. I do not like my penis exposed, so I go to a fucking toilet like a woman. It has definitely shaped my life. I think I would be a different kind of guy if I had a big penis. I would like to have a big penis.”

“I have said to my wife for the whole time we’ve been married, ‘We should pack it in and sell everything. Then we’d have enough money to live in Iowa.’ It’s always been Iowa; there’s a big transcendental meditation center in Iowa. So I’ve said, ‘We’ll go live around there. We’ll meet a lot of people who are real mellow.’ And in Iowa, you could probably get 300 acres for ten cents.

So that’s my fantasy. And I firmly believe that I’d be happy doing that.”

“Cheating is when you stick your dick into a vagina. Or when you get a hand job or a blow job—that’s cheating. Everybody has his own way of looking at what sex is. People say to me that there’s nothing wrong with having sex with other women and also being married—people I respect have said that to me. Well, maybe I’m old-fashioned, but it just seems wrong.”

“You know, I love strippers and shit—girls who come down to the radio station and take their tops off. Party girls. But would I want my daughters to do that? Probably not. I want my daughters to be nuns.”

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*Or read the interview with access to all Playboy interviews on iPlayboy.*